Luxury Properties for rent in the State of Massachusetts

This classic New England home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of...

Presented by Samantha Morel | Wallace & Co. Sotheby's International Realty

This home is located in the heart of Wianno, only minutes to Dowses Beach and the village of Osterville. The first floor offers an open floorplan including living room, dining,...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

The perfect Berkshire country retreat for large gatherings awaits you. Bring your friends to enjoy this stunning home and property on 18+ acres perched atop the Berkshire hills...

Presented by Thom Garvey | William Pitt Sotheby's International Realty

236B Smoke Valley is serene and surrounded by nature, offering peaceful mornings, beautiful sunsets, and water access right outside your door. A deep-water pier and float can...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Cape Cod summertime magic awaits at this classic shingled charmer in the heart of Wianno. Just moments from Osterville Village and Dowses beach, and superbly appointed, everything...

Presented by Ellen Valentgas | Sotheby's International Realty - Osterville Brokerage

Recently updated contemporary overlooking the farm in Katama. This 4 bedroom, 2.5 bathroom property features open living space and amazing outdoor space with private pool and...

Presented by Samantha Morel | Wallace & Co. Sotheby's International Realty

Brand new construction on Oyster Pond. This property features five bedrooms including a primary ensuite on the first and second floors. There are two additional bedrooms on the...

Presented by Samantha Morel | Wallace & Co. Sotheby's International Realty

This charming cape was just remodeled! Walk to Craigville Beach, Four Seas Ice cream, 1856 Country Store and the Library! The new kitchen is finished with quartz counters and top...

Presented by Colleen Riley | Sotheby's International Realty - Osterville Brokerage

Welcome to Seasons by the Sea! This fully remodeled Osterville home offers four bedrooms, three and a half baths and all the outdoor living space for a perfect beach vacation....

Presented by Jan Macallister | Sotheby's International Realty - Osterville Brokerage

August 2023 - Hip 1820 country home with Scandinavian interior design touches. The living room and the den with fireplace have both an abundance of natrual light from south facing...

Presented by Christian Deckert | William Pitt Sotheby's International Realty

This home sits on a unique piece of the Edgartown harbor. With balconies overlooking the harbor, your vista is forever changing. Located on the north side of Edgartown, guests can...

Presented by Samantha Morel | Wallace & Co. Sotheby's International Realty

This stunning mid-century 3-bedroom, 3.5-bathroom house is indeed a hidden gem nestled in the sought-after village of Mill River. Offering a harmonious blend of tranquility,...

Presented by Christian Deckert | William Pitt Sotheby's International Realty

Renovated and decorated by a renowned Island decorator, and featured in Architectural Digest thereafter, this gem sits on a rather unique piece of property overlooking the...

Presented by Samantha Morel | Wallace & Co. Sotheby's International Realty

Located at the end of a quiet cul-de-sac and set on 1.5 secluded acres and less than two miles from South Beach, this luxurious custom-built vacation rental offers expansive...

Presented by Samantha Morel | Wallace & Co. Sotheby's International Realty

Winter rental Available October 1 through March 31, 2026! *Owner may be flexible with dates.* $2500/month includes utilities! Tucked away in an established Centerville...

Presented by Marina Davalos | Sotheby's International Realty - Osterville Brokerage